What is the weather usually like in mid October? (Windy right?) I meant temperature wise.

Daytime temps will likely be in the 50's or 60's...probably down in the 40's at night...give or take...we often get some "Indian Summer" in October that puts daytime temps into the upper 70's.

Basically light jacket weather.

The leaves will be changing and Grant Park will be awash of autumn colors.

TRIVIA ALERT AHEAD: Chicago is known as the "Windy City" not because it is windy (which it is) but because Chicago Politicians are well known for their ability to talk for hours and hours about nothing and really fillibuster (sp?) and cause wind with their babbling.

Fans of Amusement Parks may consider making a drive up to Six Flags in Gurnee (about an hour north/northwest of Chicago)...they have "Fright Fests" in October, all the rides are decorated and the staff all walks around in costumes...

Tony & Tina's wedding is a blast (for those who dont know its like dinner theater and the setting is an actual wedding at which you are a guest...you interplay with the actors and no one knows who is an actor and a guest...wedding, reception (with buffet included), dancing.

Tommy Gun Garage - same thing but with a gangster theme

Finnegans Wake - same thing but set at a funeral

Murder Mystery - same thing but hosted on a train ride - very Agatha Christie like.

There is also a bus tour that takes you to all the places in Chicago that are supposed to be "haunted", including the alley where the St. Valentines Day Massacre took place.